


Valentine's Day Dinner Date

by Piper_Halliwell1979



Category: Supernatural
Genre: Castiel Ships It, Dean Ships It, Dinner, F/M, Fluff, Matchmaker Dean Winchester, Slow Romance, Valentine's Day
Language: English
Status: Completed
Published: 2020-02-13
Updated: 2020-02-13
Packaged: 2021-02-28 06:14:58
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 840
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22689097
Author URL: https://archiveofourown.org/users/Piper_Halliwell1979/pseuds/Piper_Halliwell1979
Summary: Dean and Cas play matchmaker for Sam and Eileen on Valentine's Day
Relationships: Eileen Leahy/Sam Winchester, saileen
Comments: 6
Kudos: 59





	Valentine's Day Dinner Date

"I don't see the 'romance' in ironing a tablecloth, Dean." Castiel rolled his eyes but continued pressing the linen.

"Dude! It's all about setting the mood. Y'know... _ ambience. _ " 

"Did you even bother asking them if they wanted all this?" The angel's eyebrow raised.

Dean huffed. "Of course not! It's...it's our gift to them, alright? We lay out the candles and romantic dinner and BOOM...Sammy wins Valentine's Day with Eileen."

"You know they're taking things slowly. This could all be a bit...overwhelming." Cas put down the iron. "Look, I want them to be happy and together, too. Maybe this is too much of a push."

"Cas...it's not like we're putting silk sheets and rose petals on Sam's bed. Okay? All we're doing is setting up a nice little in-house date and whatever happens...happens. We'll take Jack out to a movie or something so they can have some privacy."

Castiel nodded in acquiescence before turning his attention to polishing the silver candlesticks Dean had taken out to set the scene.

***

Eileen descended the steps into the war room with her bag over her shoulder. "Dean! I got your text. How can I help?" She was swept into a brotherly hug before she got a response. 

Dean pulled back then braced his hands on her shoulders. "There's not actually a case. I kinda just…"

"Dean, what's up? Oh...hey, Eileen." Sam smiled and brushed his hair back over his ear. "I didn't know you were coming over."

Eileen narrowed her eyes at Dean. He chuckled nervously. "Well you crazy kids have been working so hard lately...thought I'd treat you to a nice home cooked meal."

Sam rolled his eyes.  _ He Parent Trapped us,  _ he signed.

Eileen shrugged and shucked her bag onto the map table.  _ Free food,  _ she signed back. 

"I recognized the sign for food so…" Dean gathered them both to guide them into the seldom used formal dining room.

Castiel just finished lighting the candles. There were two complete place settings, a bottle of red wine, and a plate of chocolate covered strawberries. Cas got the points for that one when he pointed out how much Eileen loved strawberries. 

Eileen looked between the three men with wide eyes. "What is all this?"

"Happy Valentine's Day! Everything you need is in the kitchen. This big lug," Dean clapped his brother on the shoulder, "will be your server."

Sam directed bitchface #34 at him. "And you'll be out celebrating Unattached Drifter Christmas?"

"Nope. Those days are behind me, Sammy. Doing the Dad thing tonight. Me and Cas are taking Jack and making ourselves scarce. You kids have fun." Dean shot them finger guns with a smirk. He collected Cas and headed to the garage to meet Jack before Sam could say anything.

"I think it's kind of sweet," Eileen broke the silence. "Your brothers went to all this trouble...I say we enjoy it. Ooh strawberries!" She lit up and helped herself to one.

Sam's face turned into a warm smile. He held out the chair for her and poured two glasses of wine before venturing into the kitchen to see what Dean had left them. He chuckled at the salads labeled "Round One: Rabbit food." He brought the bowls out and seated himself across from Eileen.

"I um...this was all Dean. I don't want you to feel pressured or anything…"

Eileen shook her head. "Sam...it's okay," she signed along, "I like spending time with you. Things are just...complicated." She poked at her salad. "Where's the real food?"

Sam grinned. "You sure you got the right Winchester?"

She beamed back at him with a sparkle in her big brown eyes. "That depends. Who got me the strawberries?" She teased.

Sam pondered that for a moment before returning with the two covered plates. "I think I just lost more points. You got a steak and I got salmon."

At that, she giggled. "Dean's not my type. Now the pretty blue-eyed angel…"

"Hey!" Sam mocked offense before laughing with her. "Okay. This  _ is _ nice. I'm glad you're here. I..I missed you."

Eileen reached across the table for his hand. "I missed you too, Sam. You mind if I stay here tonight?"

"Please? No...expectations."

"We'll see."

***

"I don't understand. Everything is supposed to be heart-shaped for Valentine's Day and they aren't even anatomically correct."

Dean grinned. "You sound just like Cas used to, Jack. It's just a holiday some corporate desk jockey came up with to empty our wallets."

"Then why was it such a big deal for us to leave so Sam could have dinner with Eileen?" Jack tilted his head and squinted. 

"Because of that," Cas pointed at the makeshift family room. Sam had his arm around Eileen while she rested her head on his shoulder. They were relaxed and cozy on the sofa, the lights of the television flickering on them.

"They look happy," Jack concluded.

"Yeah Kid, they do. They deserve it." Dean smiled and ushered them quietly out of sight.


End file.
